Serendipity
by InspiringDreamsTVD
Summary: Elena Gilbert, 18 year old student in her senior year at Mystic Falls High School and Damon Salvatore, 20 year old student in his sophomore year at college. When they meet, there's a connection and they both feel it. Is it love? Will love conker all or will secrets and threat hold them back? AU/AH (Rating may change in future chapters)
1. Chapter 1

**Summary****: Elena Gilbert is and 18 year old student in her senior year at Mystic Falls High School and Damon Salvatore is a 20 year old student in his sophomore year at college. When they finally meet, there's a connection and they both feel it. Will love conker all or will secrets and threat hold them back? **

**I hope you will all enjoy this Delena fanfiction. Please comment/review and let me know if you enjoy it... I love and appreciate any feedback.**

**Disclaimer:**** I do not own any of The Vampire Diaries characters in this story. Ownership and respect go to L.J. Smith and the writers of TVD. Again, I DO NOT own anything, only the plot and some of my own characters that may pop up!**

**I hope you enjoy!**

**Chapter 1**

"I'm so sorry, Elena," the blonde said bringing the brunette into a tight, squeezing hug.

Elena laughed at her friends' compassion. "Caroline," Elena strained out still wrapped in her embrace, struggling to breathe. "Care, seriously, I can't breathe," she strained out again. "Let go," she demanded.

Caroline instantly released her. "Ow, sorry" she said with a giggle of sincerity. They both sat down outside the quant, vintage coffee shop where they regularly go to talk and let out all of their thoughts and feelings. "So, what happened with you and Matt, Elena? Tell me everything," the blonde insisted curiously.

Elena shrugged. "There's nothing to tell Care," she said.

Caroline arched an eyebrow questioningly. "Elena?"

Elena sighed, she knew she had to tell her everything, it was impossible to be able to even miss one little detail out because Caroline would always seem to know. "I didn't feel the same way for Matt as he did for me. Don't get me wrong, he's an amazing guy and I love him... but more as I would a brother or best friend. We didn't have enough chemistry...if any at all."

The blonde flashed her a sympathetic look, "I understand, Elena..." she trailed off for a moment but continued. "Although, he was perfect... and definitely marriage material," she smirked and sent a wink to Elena. "For when your time comes obviously," she added.

Elena rolled her eyes. "Yeah, I won't deny that about him, but I'm not ready to get married and honestly I don't think he's the type of person I would want to marry. I'm eighteen, Care, I want to live my life and have fun before I settle down. I don't even want to think about that yet." Elena explained.

"Is that the only reason... or is it that you don't know what you want yet?" Caroline questioned.

Elena sighed with an added smile. "I know what I want, Care." Caroline raised her eyebrows as a gesture for her to continue. Elena sighed and continued, "I want passion and adventure... I want a little danger. I want fun. I want a love that can completely consume me. I want to have a love that makes me feel more alive than I have ever felt. I want to feel the lust and admiration of life and love. That's what I want."

Caroline raised her eyebrows and smiled. "Well, be careful what you wish for, Elena."

"What happened?" The green eyed boy asked sitting down on his, non-identical, twin brother's bed. He watched him sitting at his desk playing with a black ball tip pen he held in his right hand.

The dreamy raven haired boy put down the pen and relaxed back in his desk chair putting his hands behind his head, relaxing. He shrugged. "I broke up with her, that's all there is to it."

The green eyed boy arched his eyebrow. "Seriously Damon... You can't keep doing this."

A frown appeared on Damon's face. "Yes, Stefan, _seriously,_ I wasn't happy with Andie...and what do you mean exactly by 'you can't keep doing this' doing what?" he asked curious by his brothers comment.

Stefan sighed. "I mean, you can't just keep picking and dropping girls whenever you're bored or aren't happy with then. It's not fair on them, Damon."

"Well, _Stefan,_ it isn't exactly fair on me either and I agree it isn't fair on them but if I went on pretending to be into someone when I'm not that's even worse and would end up hurting them more. Even if you don't see it, I am doing the right thing here brother." Damon snapped.

"I know you are Damon but I actually thought you liked Andie, you seemed like you did, and she's a lovely girl... _and _is attractive too. There wasn't anything wrong with her," he encouraged.

A frown appeared on Damon's face again. "Yeah okay she's hot and a nice person but we didn't have any... any chemistry..." He rested his feet up on top of the desk, "...well not the kind of chemistry that I want. I want passion and excitement, and I didn't have that with her. I want to be able to have fun and I want to feel happy. Someone who is fun loving, carefree, beautiful... I want someone who makes me feel _alive_. Andie didn't do that for me..." he explained and his brother's eyebrows arched up high. "I want to meet a girl who has all of that and more," Damon added.

Stefan stood up from his brothers' bed and walked towards the bedroom door. "Well I hope you find her," he said before exiting the room.

Damon sighed, "Yeah, me too brother."

XXXXXXXXXXXXXXXXXXXX

Elena walked down the crowded school hallway towards Bonnie and Caroline. She sighed when she got to them. "These crowded corridors will be one thing I definitely won't miss when we leave," she stated jokily and the two other girls laughed in agreement.

Her dark haired friend turned directly to her friend and hugged her. "How are you bearing up?" she asked with her voice full of sympathy and released Elena from her embrace.

Elena rolled her eyes and laughed kindly at her friends' sincerity. "Bonnie, I'm fine," she gave Bonnie another quick hug of reassurance.

"Really?" Caroline questioned arching her eyebrow.

Elena rolled her eyes and laughed again. "I've never felt better. I feel free and full of life. I'm just ready to have fun and live my life for _me _instead of living it for everyone else."

Bonnie and Caroline smiled proudly at their friend. They caught around her at either side of her. "That's our girl," Caroline beamed.

Elena giggled as a beaming and blissful smile invaded her entire face.

The three girls walked arm in arm towards their history class. The entered the classroom to see other students sitting in their seats and Alaric Saltzman, their teacher and Elena's Aunt Jenna's boyfriend, sat at his desk. "Morning Ric- I mean Mr Saltzman," Elena greeted and as she did Alaric looked up and smiled at her and her friends.

"Good morning Elena, Bonnie, Caroline," he greeted them.

"Morning Sir," they said in unison as they all took their regular desks in the middle of the classroom next to each other.

When everyone had entered the classroom and sat in their seats Alaric stood up from his desk chair and walked around to the front, leaning on it. "Morning everyone, first of all I want to let you all know that the dance committee need volunteers to help with the Halloween dance. So if anyone is interested please see our very own Miss Caroline Forbes," he gestured towards Caroline who smiled at him. "Secondly, I have an assignment for you all to do. It's an individual task where I want you to focus on the Civil War era and I want you to write a diary entry for someone from the time. You can decide the type of character you do however your entry must include facts from research you have done. Is everyone okay with that?" He asked and the whole class nodded. "Are there any questions about it?" Alaric looked around the classroom and nobody had a question. "No, great, let's get this lesson started then."

Damon walked into the lecture hall where Professor Paul Hansen, his history tutor preparing for today's lecture. As Damon walked to a seat in the third row, Professor Hansen glanced up to greet him. "Good morning, Salvatore. Nice to see you here bright and early," he smiled.

Damon smirked, "Morning Paul, you know I simply can't miss your amazing lectures," he said with sarcasm in his tone.

Paul rolled his eyes. "Always the charmer, Damon," he chuckled. The other students began to enter the lecture hall and take their seats. Paul looked up counting heads and briefly clapped his hands together. "Great, everyone's here, let's get started then," he said as he began to show a presentation and talk through it while the class took notes.

As Damon walked out of the lecture hall his phone began to buzz. Damon glanced down at the caller ID, _Mason. _"Yeah, what's up?"

"Hey, nothing much on my break, you busy?" he asked.

"No, just came out of a lecture, what did you want?" Damon asked curiously.

Mason cleared his throat with a cough. "Yeah, I was just checking if you were coming out tonight?"

Damon walked into the campus cafe and waited in the line. "Yeah sure," he approached the counter. "Hold on a minute," he looked at the board behind the counter and looked at the woman to order. "Yeah, one regular coffee please, black and to go, thanks." He said and winked at the woman before she turned to make it. "Yeah sorry, Mas, uh, what time tonight?" he asked.

"You took long enough," he chuckled, "7:30, the Mystic Grill, yeah?"

Damon took the coffee from the woman and thanked her with a smile and a wink before leaving the cafe. "Yeah great," he confirmed.

"Maybe it'll take your mind off Andie."

"Man, doesn't even bother me. Hey I'll see you later, busy man, things to do and what not," he said sitting at one of the benched under a big oak tree.

Mason chuckled down the phone. "Yeah, see you later."

Damon hung up the phone and took one of his books out of his backpack and began to read it.

Elena, Caroline and Bonnie were sat at the table in the crowded cafeteria. "So, is there any new gossip?" Caroline asked cheekily.

"Caroline, what is it with you and gossip?" Elena laughed.

Caroline shrugs her shoulders. "I don't know I just like knowing all the new news, that's all."

Bonnie and Elena giggled. "You should be a reporter or something," Bonnie suggested with a laugh.

Caroline raised an eyebrow. "Well I was considering broadcast journalism," she said with a smirk to show Elena and Bonnie she was joking. "Anyway, I just remembered I have some news."

"What a surprise," Bonnie murmured under her breath.

Caroline leaned closer to them on the table. "Tyler Lockwood is having a party next week and we totally have to go."

"What day? What time?" Bonnie asked.

"Next Friday at eight, you two up for it?" she asked perkily.

"Yeah, Tyler always throws amazing parties, definitely will be there." Elena confirmed.

Bonnie looked over Elena's shoulder and saw Matt walking towards them and quickly gave Elena a warning look. Elena instantly knew it was something to do with Matt. Matt reached their table and stood by Elena with a tray of food. "Hey guys,"

"Hey," Caroline and Bonnie said in unison.

Elena hesitated to look up and when she did she meant his sweet boy like baby blue eyes. "Hi Matt," she greeted after a silent moment.

Matt stared directly at Elena, which made her uncomfortable but tried her best to hide it. "Can I talk to you for a moment?" he asked.

Elena glanced at Caroline and Bonnie who briefly widened their eyes in code to say yes. Elena turned back to Matt and stood up, "Sure, here or in private?" she asked giving him the choice wanting him to be comfortable to talk to her.

"If you don't mind, I'd kinda like a word with you in private," he hesitated. "If that's okay," he added quickly looking at Bonnie and Caroline.

Elena smiled friendly and stood up. "Of course, its fine," she turned back to Bonnie and Caroline giving the sign she'd be right back as she followed Matt out of the cafeteria and into the currently empty school hallway. Matt halted and turned to face Elena who had stopped walking. "I just want to let you know that I'm not here to ask to go back out with you, I'm not that guy and I respect your choice. I just want to make sure that there isn't going to be any awkwardness between us. I don't want to lose you Elena, as a friend I mean."

Elena smiled sincerely at Matt and caught around him in a friendly hug. "You won't lose me Matt, we were friends before and we can be friends now. I don't want to lose you either because your friendship is so important to me."

They both released each other from the friendly embrace and Matt smiled. "Thank you, Elena. I was so worried that things would be awkward. Trust me, I wasn't over the moon about the break up and I still love you, I can't get over that straight away but I understand that you didn't feel the same and weren't happy with us that way. I would rather you be happy than just stay with me because you feel guilty- it's better for both of us."

"I'm so glad that you understand Matt and I understand that it'll take a while to get over this but I still love you but more as a brother and friend. You're an amazing guy and any girl would be lucky to have you, thank you for understanding." Elena smiled and gave him one last hug before heading back into the cafeteria, rejoining Bonnie and Caroline.

**I hope you all enjoyed the story so far. Please give feedback, I love to hear what you have to say and if there is anything I could improve on. Also I will take on any ideas you may have for the story and see if I can fit them in. **

**Let me know if you like it and want me to carry on with this story. I know there wasn't any Delena in this chapter but it was the introductory chapter. So if I continue there might be some next chapter or chapter 3...but only if you want me to continue.**

**Hope you enjoyed! Chapter 2 will be updated soon!**


	2. Chapter 2

**Here's chapter 2, hope you enjoy it! **

**Sorry I've kept you waiting but I've had a lot of college work to do as well but I'm trying to keep the updates weekly maybe even two in the same week if I can.**

**You're probably waiting for the Delena goodness to start. This was basically a filler chapter because next chapter is when they meet. I also wanted to give an in site to what both of their lives are like before they meet and how them meeting changes a lot of things. Also thank you for everyone who is reading and the reviews, I'm glad you wanted more because I really like this story idea!**

**Anyway, enjoy!**

**Chapter 2**

Damon entered the Grill and saw Mason sitting at the bar with two glasses of scotch in front of him. Damon smirked to himself and walked over to the bar, sitting in the stool next to Mason. "You bought me a drink, how kind," he said sarcastically.

Mason chuckled. "Yeah right, their mine. You're under age," he joked.

Damon rolled his eyes. "Not for long," he stated. "I can get served now anyway."

Mason scoffed. "Ha- I'd like to see you try," he challenged.

Damon arched one of his eyebrows and quirked up his lip. "Challenge expected." Damon called over the bartended from the other end of the bar, lucky for him a woman was working. He smiled flirtatiously at her narrowing his eyes drawing her in. She began to blush, "What can I get you?" she asked.

"Hello..." he said huskily looking at her name tag, "... Jessica. What a beautiful name." He stated leaning his chin in one hand smirking.

Jessica smiled shyly, "Thank you. So, what can I get for you?" she asked again.

"Bourbon, please Jessica." Damon's eyes remained on hers and she felt weak under his gaze. Damon had that affect on woman.

"Sure, I'll just get it for you," she smiled and went to get his drink.

Mason leaned closer to Damon and whispered. "That's cheating," he declared.

Damon turned to look at him with a smug smile on his face. "No, you bet I couldn't get served and I did. You never put out any rules, so technically, I won."

Mason shrugged in defeat. "Okay, but next time we do this when there's a man working here, see if you can get served then."

Damon smirked as Jessica brought back his drink, "Deal."

Elena sauntered into her open planned kitchen and dining room. An oak wooden table stood at the far left side of the room and on the right was a decent sized kitchen; marble counters, an island in the centre and bar stools around one side.

She opened the fridge, pulled out a jug of ice tea and opened the cupboard next door for a glass. Elena moved to sit on one of the stools and sat down letting out a sigh. At that moment Jenna walked in through the front door. "Elena!" she called out. "Are you home?"

Elena stood up and walked into the hall. "Yeah, I'm here Jenna, everything okay?" she asked seeing a very stressed aunt stood in front of her.

Jenna whipped the back of her hand along her forehead and put her brown, leather handbag at the bottom of the stairs. "Yeah, just a little stressed."

"I can see that, sit in the living room I'll bring you a coffee," Elena insisted.

Jenna smiled gratefully at her niece. "Thank you," she said before descending into the living room while Elena went to make her Aunt some coffee.

A few minutes later Elena entered the living room with a cream mug in her hand: hot steam pouring out of it. Her Aunt was sat on the couch, one leg crossed over the other staring at the television however not paying attention to the program viewing. "Here you go, Aunt Jenna," Elena handed her Aunt the mug and sat down next to her.

Jenna smiled. "Thanks, I need this."

"What's got you so stressed out?" Elena asked concern apparent in her voice.

Jenna let out a contented sigh from taking a sip of coffee and balanced the mug on her knee, one hand still wrapped around it. "I have an essay to write, I'm moving in with Ric and honestly, I'm worried about you and Jeremy. I know you're eighteen but are you sure you'll be okay here by yourself, taking care of Jeremy?"

Elena placed her hand on Jenna's shoulder in assurance. "Jenna, Jeremy and I will be fine I promise. I've been here alone with Jeremy since you've been staying on campus, I've been taking care of him and we have both been fine. I'm an adult now Jenna, I can handle this," Elena sent her Aunt a reassuring smile.

Jenna sighed. "I know, I know but you're still in high school, you have finals to think about and taking care of Jeremy on top of that..." she trailed off.

Elena laughed sincerely. "Jenna, I know you trust me and Jeremy. I know you trust me. You wouldn't have agreed to move in with Ric unless you trusted us, unless you trusted me. You're having second thoughts but only because you're worried about us and that's normal. You're moving five minutes away not five hundred miles, it's not like you can't come and check up on us."

Jenna smiled; Elena was always a smooth talker, in any situation. "You're right, I trust you and I can always come and see you. Remember if you ever need anything call me, I will drop everything. Promise me if you ever need help with anything you'll call me or Ric; we'll be here for you."

Elena rolled her eyes and hugged her Aunt. "Yes, Jenna, I promise. I will call you; we will call you if we need anything."

Jenna smiled and moved her now empty coffee mug to the coffee table. "So, how was your day?" she asked.

Elena leaned, resting her head on the back of the couch. "Same old, really, nothing exciting ever happens."

"How are Bonnie and Caroline?"

Elena giggled. "Yeah they're fine, Caroline's her bubbly self and Bonnie is herself. We're all good," she assured.

"Good," Jenna paused for a moment before continuing. "A touchier subject, how are you and Matt? Still broken up or have you sorted things?"

"Still broken up and we are staying that way. I don't share his feelings and if I pretended to feel the same way it would hurt him more later on and I care too much about him to do that, so I set him free. I can't be selfish with the people I care about. God, I can't be selfish with anyone," she laughed at herself for a moment.

"I understand, you did the best thing for both of you. Is he okay with it?"

"Well, he understood why I broke up with him but I think he still loves me... I don't think, I know he still loves me but I'm sure after a while it'll get easier for him. He deserves someone who feels the same way, not unrequited love, that's unfair to both of us."

Jenna wrapped one arm around her shoulder. "You did the right thing Elena. Believe me, he will understand and he'll get past this. He'll realise you did it for him because you care."

"I hope so, I still want us to remain friends, like before and I don't want us to have any awkwardness. I still love him but I'm not _in _love with him. I love him like I love Jeremy, you, Bonnie, Caroline; he's family."

Jenna smiled proudly. "I'm so proud of you, Elena. You're maturing, turning into a beautiful and independent woman and watching you grow like this has been a gift. You deserve everything you want out of life, happiness. You and Jeremy have been through so much, this whole family has and to watch you remain strong and fight through this makes me so proud of you. Grayson and Miranda would be looking down at you and Jeremy and saying how amazing you both turned out and how you're both beautiful people. They would be so proud of you."

A small tear drop escaped Elena's eye, hanging on her eyelashes for a moment before dropping to her hand. "Thank you so much, Jenna. For looking out for us, I bet mom and dad would be proud of you too. You grew up with us and I know if you weren't here, we wouldn't have made it through so thank you."

Jenna's eyes began to water and she kissed the top of Elena's head. "I'll always be here for you both, Elena."

Elena came out of her bathroom, hair pulled up into a messy bun; face clear of her makeup and wearing her pink, green and white polka dot pyjama shorts with a pink tank top. Jenna had left a few hours ago and Elena was ready to go to bed. She pulled back the quilt of her bed when her phone began to ring from the dressing table. Elena darted over to it and saw it was Bonnie. "Hey Bonnie, you okay?" she asked.

"Yeah I'm fine Elena, are you okay?" Bonnie asked in return.

"Yeah, so what's up?"

"Oh, I was wondering if you wanted to go to the library Saturday to do research for that history assignment..."

"Yeah sure, it'll be easier with the three of us there."

"Great, I'll let Caroline know," Bonnie stated. "So has Jenna officially moved out yet?"

Elena walked over to her bed and sat on the edge of it. "Yep, Jenna and Ric are officially living together and Jeremy and I are living here."

"That's pretty cool you have a house to yourselves, you're basically living alone."

"Well the house was left to me and Jeremy so it is ours and yeah it is pretty cool, I'll miss Jenna being in the house but she said she'll be over a lot to check up on us."

"Yeah, it's not like she's moving to a different country."

"Yeah, she's been stressed lately with moving out and college work but I'm sure when she's settled everything will be fine."

"And it's not like you have been without her, she went to stay on campus too, didn't she, also you can always call me if you get lonely, we can throw a party," Bonnie suggested with a teasing tone in her voice.

Elena laughed. "Yeah," she said sarcastically. "Hey, I'm really tired I'm going to go to bed, I'll see you tomorrow."

A yawn came down the phone from Bonnie. "Me too actually, I'll see you tomorrow. Good night."

"Good night, Bonnie," Elena hung up the phone and plugged the charger into it, leaving it on the desk. Elena walked back over to her bed and climbed in, snuggling up underneath the covers before falling asleep into a graceful slumber.

Damon walked up his drive way after spending the evening at the Grill with Mason. He began to head towards the stairs when he noticed his father walking down them holding two suitcases in each hand. Damon frowned in confusion, "Dad, what are you doing?" he asked.

Giuseppe placed the suitcases at the bottom of the stairs and glared his eyes into Damon's. "I'm leaving, I've been asked to go to Italy, government reasons can't go into detail, but I'll give you all of my contact information and where I'm living... Also, I have left one million dollars in an account for both you and Stefan, considering you're both adults now you can live here alone or get your own place whatever."

Damon's frown disappeared and his eyebrows rose in shock. "What, you're leaving and you weren't going to tell us until now?" anger was beginning to boil up inside Damon.

"I've told you now, I could have left only leaving you a letter but I'm here telling you. I've set you up, you'll be fine." Giuseppe picked the suitcases back up and walked towards the front door.

"Oh, I know I will be," Damon snapped. "Stefan will be too, I just can't believe you're only telling us now. Actually yes I can believe that, your fickle and self absorbed," clear anger and frustration could be heard in his voice.

Giuseppe dropped the suitcases and turned to face Damon shooting murdering eyes at him. "Don't you dare disrespect me in that way," he screamed. "I am your father, you show me some respect."

Damon stepped forward towards Giuseppe shooting daggers back at him. "You don't deserve my respect, _father_, if I can even call you that. Thanks for the money and stuff, I'd say I'm sad to see you go but that would be a lie," he growled.

"Goodbye, Damon, I've already told Stefan, at least he didn't disrespect me, he's in his room. Don't expect to see me anytime soon; I won't be back for a while." Giuseppe picked the suitcases back up and stormed out of the door.

"Good riddens, _father_," Damon spat before heading up the stairs towards his bedroom. He passed Giuseppe's room and peered inside to see everything apart from a bed had gone. It was like his father had never even lived there. Damon scoffed and carried on to his bedroom, cursing under his breath, and slamming the door shut behind him.

**I hope you enjoyed the chapter. Some Elena and Jenna bonding, I hope you liked that and also, Damon and Mason at the Grill. You now know their father is a d*** and doesn't give a damn about them. There is more behind that too which I plan to tell later on.**

**Anyway, the next chapter is where Damon and Elena meet for the first time and the reason I named the story Serendipity. The word serendipity (for those who don't know already) basically means a 'happy accident' or 'pleasant surprise' and that is what Delena's meeting is...**

**Chapter 3 will be up soon! **


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